NZ554817A - 3-Phenyl-pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto - Google Patents

Info

Publication number

NZ554817A

NZ554817A NZ554817A NZ55481705A NZ554817A NZ 554817 A NZ554817 A NZ 554817A NZ 554817 A NZ554817 A NZ 554817A NZ 55481705 A NZ55481705 A NZ 55481705A NZ 554817 A NZ554817 A NZ 554817A

Authority

NZ

New Zealand

Prior art keywords

phenyl

methyl

pyrazol

compound

ethoxy

Prior art date

2004-11-19

Links

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• Global Dossier
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 140
• 238000011282 treatment Methods 0.000 title claims abstract description 134
• 208000035475 disorder Diseases 0.000 title claims abstract description 117
• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title abstract description 29
• 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title abstract description 25
• OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical class N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 title abstract description 23
• 150000001875 compounds Chemical class 0.000 claims abstract description 410
• 150000003839 salts Chemical class 0.000 claims abstract description 110
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 108
• 239000012453 solvate Substances 0.000 claims abstract description 88
• 230000001404 mediated effect Effects 0.000 claims abstract description 45
• 208000006011 Stroke Diseases 0.000 claims abstract description 20
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 19
• 208000010125 myocardial infarction Diseases 0.000 claims abstract description 14
• 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 12
• 208000029078 coronary artery disease Diseases 0.000 claims abstract description 9
• -1 C]_6 alkylureyl Chemical group 0.000 claims description 489
• 125000000217 alkyl group Chemical group 0.000 claims description 150
• 239000004202 carbamide Substances 0.000 claims description 139
• 238000000034 method Methods 0.000 claims description 135
• 125000001424 substituent group Chemical group 0.000 claims description 108
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 93
• 229910052736 halogen Inorganic materials 0.000 claims description 79
• 150000002367 halogens Chemical class 0.000 claims description 79
• 239000003814 drug Substances 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
• 125000002252 acyl group Chemical group 0.000 claims description 71
• 125000004423 acyloxy group Chemical group 0.000 claims description 70
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 65
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 63
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
• 239000000203 mixture Substances 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
• 125000001188 haloalkyl group Chemical group 0.000 claims description 57
• 238000004519 manufacturing process Methods 0.000 claims description 54
• 208000019116 sleep disease Diseases 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
• 150000003857 carboxamides Chemical class 0.000 claims description 46
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 43
• 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 39
• 125000003282 alkyl amino group Chemical group 0.000 claims description 39
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 39
• 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 38
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 34
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 208000020685 sleep-wake disease Diseases 0.000 claims description 32
• 125000003342 alkenyl group Chemical group 0.000 claims description 31
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 241001465754 Metazoa Species 0.000 claims description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
• 206010003658 Atrial Fibrillation Diseases 0.000 claims description 20
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 20
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 20
• 206010013980 Dyssomnias Diseases 0.000 claims description 18
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 17
• 230000035602 clotting Effects 0.000 claims description 17
• 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 claims description 17
• 206010012601 diabetes mellitus Diseases 0.000 claims description 16
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 15
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
• 125000005277 alkyl imino group Chemical group 0.000 claims description 13
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• 150000003573 thiols Chemical class 0.000 claims description 13
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• 125000002947 alkylene group Chemical group 0.000 claims description 11
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 10
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 10
• 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 10
• 229940124530 sulfonamide Drugs 0.000 claims description 10
• 150000003456 sulfonamides Chemical class 0.000 claims description 10
• 208000002193 Pain Diseases 0.000 claims description 9
• 238000002399 angioplasty Methods 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 230000036407 pain Effects 0.000 claims description 9
• 238000001356 surgical procedure Methods 0.000 claims description 9
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 9
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 9
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 8
• 206010020772 Hypertension Diseases 0.000 claims description 8
• 208000006199 Parasomnias Diseases 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 6
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 6
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• ADZOFZRDWPGJCH-UHFFFAOYSA-N n-[3-(2-methylpyrazol-3-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-4-(trifluoromethyl)benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(F)(F)F)=CC=C1OCCN1CCCC1 ADZOFZRDWPGJCH-UHFFFAOYSA-N 0.000 claims description 5
• 125000000466 oxiranyl group Chemical group 0.000 claims description 5
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• DURLHNRJANXKOX-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]cyclopropanecarboxamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C2CC2)=CC=C1OCCN1CCOCC1 DURLHNRJANXKOX-UHFFFAOYSA-N 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• MKVQRTYMROUEJT-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[4-(2-imidazol-1-ylethoxy)-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C(=CC(F)=CC=2)F)=CC=C1OCCN1C=NC=C1 MKVQRTYMROUEJT-UHFFFAOYSA-N 0.000 claims description 3
• DTZPPHXYPZBDMZ-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(3-hydroxyazetidin-1-yl)ethoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OCCN1CC(O)C1 DTZPPHXYPZBDMZ-UHFFFAOYSA-N 0.000 claims description 3
• BMSMOYJGZAKUNL-UHFFFAOYSA-N 2,4-difluoro-n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C(=CC(F)=CC=2)F)=CC=C1OCCN1CCOCC1 BMSMOYJGZAKUNL-UHFFFAOYSA-N 0.000 claims description 3
• UNHNPMBOCGFCOO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C=C(C(OCCN3CCOCC3)=CC=2)C=2N(N=CC=2)C)=C1 UNHNPMBOCGFCOO-UHFFFAOYSA-N 0.000 claims description 3
• GRKDZPGEIINYTL-UHFFFAOYSA-N 2-(3-methylphenyl)-n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C=C(C(OCCN3CCOCC3)=CC=2)C=2N(N=CC=2)C)=C1 GRKDZPGEIINYTL-UHFFFAOYSA-N 0.000 claims description 3
• QXUZOMBBTXORFM-UHFFFAOYSA-N 3,4-difluoro-n-[4-[2-(2-methylpiperidin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound CC1CCCCN1CCOC(C(=C1)C=2N(N=CC=2)C)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1 QXUZOMBBTXORFM-UHFFFAOYSA-N 0.000 claims description 3
• RHSHFZVUUPQGMQ-UHFFFAOYSA-N 3-chloro-4-fluoro-n-[4-[2-(4-fluoropiperidin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(Cl)C(F)=CC=2)=CC=C1OCCN1CCC(F)CC1 RHSHFZVUUPQGMQ-UHFFFAOYSA-N 0.000 claims description 3
• MHKOGYOMSFQKGL-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-4-(trifluoromethyl)benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C(=CC=2)C(F)(F)F)=CC=C1OCCN1CCCC1 MHKOGYOMSFQKGL-UHFFFAOYSA-N 0.000 claims description 3
• UGVXKTMVLNTYDE-UHFFFAOYSA-N 3-fluoro-n-[4-[2-(4-formylpiperazin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCN1CCN(C=O)CC1 UGVXKTMVLNTYDE-UHFFFAOYSA-N 0.000 claims description 3
• WNTOUHDGTGAODA-UHFFFAOYSA-N 4-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=CC(F)=CC=2)=CC=C1OCCN1CCOCC1 WNTOUHDGTGAODA-UHFFFAOYSA-N 0.000 claims description 3
• 125000005605 benzo group Chemical group 0.000 claims description 3
• XHXMQSPBUDVSJW-UHFFFAOYSA-N n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)CC=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCN1CCOCC1 XHXMQSPBUDVSJW-UHFFFAOYSA-N 0.000 claims description 3
• ZVASNPMAFOSLLM-UHFFFAOYSA-N n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-2-phenylacetamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)CC=2C=CC=CC=2)=CC=C1OCCN1CCOCC1 ZVASNPMAFOSLLM-UHFFFAOYSA-N 0.000 claims description 3
• HQUFWKLMOPWCFI-UHFFFAOYSA-N n-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-4-(trifluoromethyl)benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(F)(F)F)=CC=C1OCCN1CCOCC1 HQUFWKLMOPWCFI-UHFFFAOYSA-N 0.000 claims description 3
• UAVPDLMEWXPRFE-UHFFFAOYSA-N n-[3-(2-methylpyrazol-3-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCN1CCCC1 UAVPDLMEWXPRFE-UHFFFAOYSA-N 0.000 claims description 3
• KWSSPZDNVPANIP-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(2-piperidin-1-ylethoxy)phenyl]-1,3-benzoxazol-2-amine Chemical compound CN1N=CC(Br)=C1C1=CC(NC=2OC3=CC=CC=C3N=2)=CC=C1OCCN1CCCCC1 KWSSPZDNVPANIP-UHFFFAOYSA-N 0.000 claims description 3
• RQPPPOLYBAPKQX-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-fluorobenzamide Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCN1CCCC1 RQPPPOLYBAPKQX-UHFFFAOYSA-N 0.000 claims description 3
• MTXQEEGDHLIKDC-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl]-3,4-difluorobenzamide Chemical compound CC1CCCN1CCOC(C(=C1)C=2N(N=CC=2Br)C)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1 MTXQEEGDHLIKDC-UHFFFAOYSA-N 0.000 claims description 3
• CKXWHKSLQPYWHH-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(3-methoxyazetidin-1-yl)ethoxy]phenyl]-2-(4-chlorophenyl)acetamide Chemical compound C1C(OC)CN1CCOC(C(=C1)C=2N(N=CC=2Br)C)=CC=C1NC(=O)CC1=CC=C(Cl)C=C1 CKXWHKSLQPYWHH-UHFFFAOYSA-N 0.000 claims description 3
• VSLJHEYDDRFDDK-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(3-methoxyazetidin-1-yl)ethoxy]phenyl]-3-methylbutanamide Chemical compound C1C(OC)CN1CCOC1=CC=C(NC(=O)CC(C)C)C=C1C1=C(Br)C=NN1C VSLJHEYDDRFDDK-UHFFFAOYSA-N 0.000 claims description 3
• SYJVABDKKVMFJH-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenyl]-3-fluorobenzamide Chemical compound C1CC(OC)CCN1CCOC(C(=C1)C=2N(N=CC=2Br)C)=CC=C1NC(=O)C1=CC=CC(F)=C1 SYJVABDKKVMFJH-UHFFFAOYSA-N 0.000 claims description 3
• KLTABUVAKYYSMN-UHFFFAOYSA-N n-[3-(4-bromo-2-methylpyrazol-3-yl)-4-piperidin-3-yloxyphenyl]-4-fluorobenzamide Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)C=2C=CC(F)=CC=2)=CC=C1OC1CNCCC1 KLTABUVAKYYSMN-UHFFFAOYSA-N 0.000 claims description 3
• WGKRADSEURUAQR-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-(1-methylpiperidin-4-yl)oxyphenyl]-4-fluoro-3-methylbenzamide Chemical compound C1CN(C)CCC1OC(C(=C1)C=2N(N=CC=2Cl)C)=CC=C1NC(=O)C1=CC=C(F)C(C)=C1 WGKRADSEURUAQR-UHFFFAOYSA-N 0.000 claims description 3
• SIUXBYBGJLREKE-UHFFFAOYSA-N n-[4-[2-(3,3-difluoropyrrolidin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-4-fluoro-3-methylbenzamide Chemical compound C1=C(F)C(C)=CC(C(=O)NC=2C=C(C(OCCN3CC(F)(F)CC3)=CC=2)C=2N(N=CC=2)C)=C1 SIUXBYBGJLREKE-UHFFFAOYSA-N 0.000 claims description 3
• XCOPUDSDUWDMIU-UHFFFAOYSA-N n-[4-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-fluorobenzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCN1CCC(F)(F)CC1 XCOPUDSDUWDMIU-UHFFFAOYSA-N 0.000 claims description 3
• CMBGAERCAUPMJB-UHFFFAOYSA-N n-[4-[2-(4-acetylpiperazin-1-yl)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCN3CCN(CC3)C(C)=O)=CC=2)C=2N(N=CC=2)C)=C1 CMBGAERCAUPMJB-UHFFFAOYSA-N 0.000 claims description 3
• VZYHLQAZSGIASG-UHFFFAOYSA-N propan-2-yl n-[4-[2-(azepan-1-yl)ethoxy]-3-(4-bromo-2-methylpyrazol-3-yl)phenyl]carbamate Chemical compound BrC=1C=NN(C)C=1C1=CC(NC(=O)OC(C)C)=CC=C1OCCN1CCCCCC1 VZYHLQAZSGIASG-UHFFFAOYSA-N 0.000 claims description 3
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